Organic Chem. I. Summer 2011, Midterm-2, Prof.

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Clearly indicate your answers in the spaces provided; if we have to guess as to what or where your answer is, it's wrong. Make sure your name is on each page of the examination; the management is not responsible for lost pages. Your signature above is your assurance that you have worked independently. You are strongly advised to read the exam through completely before you begin. Total # of Questions: 22 x 3.5 pts = 77 pts Short answer questions: 26 pts

1. What is the major product of the reaction, (CH3)3COK ? (CH3)3COH heat Br A) (CH3)2C=C(CH3)2 B) (CH3)3CCH=CH2 C) (CH3)2C=CHCH3

D) (CH3)2C=CHCH2CH3 E) None of these

2. By analyzing the starting material and the product(s), the following reaction is possibly an example of what type of mechanism?

+
Br N3 N3

A) SN1

B) SN2

C) E1

D) E2

E) More than one of the above

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3. I and II are:
H H3CH2C Br OH Cl CH2CH2CH3 Cl HO CH2CH2CH3 Br H CH2CH3

I A) constitutional isomers. B) enantiomers. C) identical.

II D) diastereomers. E) not isomeric.

4. What is the major product for the following reaction?

a. BH3:THF b. H2O2, NaOH

A)

OH

D)
+ enantiomer
O

+ HCHO
E)
OH

B)

C)
OH

5. Which of the following carbocations would NOT be likely to undergo rearrangement? CH3 D) A) CH3CHCHCH3

B)

CH3 CH3

E)

CH3CHCH2 CH3

CH3CHCCH3 CH3
C)

CH3CCHCH2CH3 CH3

CH3 CH3CCH2CH3

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6. What would be the major product(s) of the following reaction?

CH3O / CH3OH 55oC

H3C H

CH3 Br

H3C H

CH3 OCH3

H3C H

OCH3 CH3

II

H3C

CH3

H3C

A) I

III B) II

C) III and IV

IV D) I and II

E) All of the above

7. What is the major product for the following reaction?

a. Hg(O2CCF3)2, CH3OH b. NaBH4, NaOH

A)
+ enantiomer
O

D)

B)
+ enantiomer
O OH

E)

None of the above

C)

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8. The compounds whose molecules are shown below would have:

CH3 H H F F CH3 F H3C H CH3 H F

A) the same melting point. B) different melting points. C) equal but opposite optical rotations.

D) More than one of the above E) None of the above

9. Which of the following reactions would yield 2-pentyne? I A) NaNH2 B) C)

Br

(1 mol) NaNH2
(1 mol)

Br

CH3OH
Br

D)
OH

HA heat
Br

E)

NaOC2H5 C2H5OH

10. What is the major product for the following reaction sequence? 1a. NaNH2, NH3 (liq.) 1b. CH3CH2CH2Br

2a. Li, CH3CH2NH2 2b. NH4Cl A)

CH3CH2CH2Br

D)

B) C)

E)

None of the above

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11. What will be the major product of the following reaction? 85% H3PO4 ? heat
OH

A)

D)

B)

E)

C)

12. Consider the SN2 reaction of 1-chloro-5-methylhexane with CN ion.

Cl

NaCN

CN

NaCl

Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both 1-chloro-5-methylhexane and CN ion? A) No effect. D) It would increase the rate four times. B) It would double the rate. E) It would increase the rate six times. C) It would triple the rate.

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13. What is the major product for the following reaction?

a. BH3:THF b. H2O2, NaOH

A)
+ enantiomer
OH

D)
OH

B)
H

OH O

E)
+ enantiomer
O

OH

C)
+ enantiomer
OH

14. The major product of the following reaction would be:

C H 2C l H CH3 OCH3

OH SN2

C H 2O H H 3C O CH3 H H

C H 2O H OCH3 CH3

I
C H 2C l HO CH3 H H

II
C H 2C l OH CH3

III

IV

A) I

B) II

C) III

D) IV

E) An equimolar mixture of I and II.

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15. What is the major product for the following reaction?

HBr
A)
+ enantiomer
Br

B)
+ enantiomer
Br Br

C) D)

+ enantiomer

+ enantiomer
Br

E)

More than one of the above

16. What is the major product of the following reaction sequence? 1. HI

2. t-BuOK, t-BuOH

A)

D)

B) C)

E)

More than one of the above

17. Which is the strongest nucleophile? A) OHB) CH3CH2OC) D) CH3CH2OH E) H2O

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18. Predict the product(s) for the following reaction sequence. 1. NaI, acetone
Cl

A)

2. CH3CO2Na, CH3CO2H D)

B)
O O

E)

A mixture of A) and D)

C)
O O

19. Which statement is not true for a meso compound? A) The specific rotation is 0. B) There are one or more planes of symmetry. C) A single molecule is identical to its mirror image. D) More than one stereogenic center must be present. E) The stereochemical labels, (R) and (S), must be identical for each stereogenic center.

20. The molecules below are:

CH3 Cl Br F Br Cl F CH3

II I A) constitutional isomers. B) enantiomers. C) diastereomers.

D) identical. E) None of these

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21. The correct IUPAC name for the following compound is:
Cl

Br

A) B) C) D) E)

(E)-2-Bromo-3-chloro-5-methyl-2-hexene (E)-2-Bromo-3-chloro-5-methyl-3-hexene (Z)-2-Bromo-3-chloro-5-methyl-3-hexene (Z)-2-Bromo-3-chloro-5-methyl-2-hexene (E)-2-Methyl-5-bromo-4-chloro-4-hexene

22. What can be said with certainty if a compound has [] 25 = -9.25 ? D A) The compound has the (S) configuration. B) The compound has the (R) configuration. C) The compound is not a meso form. D) The compound possesses only one stereogenic center. E) The compound has an optical purity of less than 100%.

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Answer Key
1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22.

B A D E C C D B B C A D E B C B B C E D A C

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